One-Pot and Regioselective Gold-Catalyzed Synthesis of 2-Imidazolyl-1-pyrazolylbenzenes from 1-Propargyl-1H-benzotriazoles, Alkynes and Nitriles through α-Imino Gold(I) Carbene Complexes

A three‐component gold(I)‐catalyzed synthesis of 2‐imidazoyl‐1‐pyrazolylbenzenes from 1‐propargyl‐1H‐benzotriazoles is described here. Initially the benzotriazole derivative suffers an intramolecular 5‐endo‐dig cyclization to form a triazapentalene. This dipolar compound is able to perform an interm...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2016-04, Vol.358 (9), p.1398-1403
Main Authors: González, Jairo, Santamaría, Javier, Suárez-Sobrino, Ángel L., Ballesteros, Alfredo
Format: Article
Language:English
Subjects:
Alkynes
Benzotriazole
Carbenes
Derivatives
gold catalysis
imidazoles
iminocarbenes
Nitriles
Pyrazole
pyrazoles
Synthesis
Triazoles
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Summary:A three‐component gold(I)‐catalyzed synthesis of 2‐imidazoyl‐1‐pyrazolylbenzenes from 1‐propargyl‐1H‐benzotriazoles is described here. Initially the benzotriazole derivative suffers an intramolecular 5‐endo‐dig cyclization to form a triazapentalene. This dipolar compound is able to perform an intermolecular and regioselective attack to a gold‐activated alkyne. After triazole breakage, the pyrazole ring and an α‐imino gold carbene complex are formed. Finally, the iminocarbene is captured by a nitrile to form an imidazole ring.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201600022